Inter-oxa-PGD1 compounds

ABSTRACT

Prostaglandin analogs with the following cyclopentane ring structure: ##STR1## are disclosed along with intermediates useful in their preparation and processes for their preparation. These analogs are useful for the same pharmacological purposes as the prostaglandins, particularly and especially as blood platelet aggregation inhibitors.

The present application is a divisional application of Ser. No. 614,242,filed Sept. 17, 1975, now issued as U.S. Pat. No. 4,016,184, on Apr. 5,1977.

The present invention relates to prostaglandin analogs for which theessential material constituting a disclosure therefor is incorporated byreference here from U.S. Pat. No. 4,016,184, issued Apr. 5, 1977.

I claim:
 1. A prostaglandin analog of the formula ##STR2## wherein Y iscis-CH═CH-- or trans-CH═CH--; wherein m is 1 to 5, inclusive;Wherein M₁is ##STR3## wherein R₅ and R₆ are hydrogen or methyl, with the provisothat one of R₅ and R₆ is methyl only when the other is hydrogen; WhereinL₁ is ##STR4## or a mixture of ##STR5## wherein R₃ and R₄ are hydrogen,methyl, or fluoro, being the same or different, with the proviso thatone of R₃ and R₄ is fluoro only when the other is hydrogen or fluoro;Wherein R₁ is hydrogen, alkyl of one to 12 carbon atoms, inclusive,cycloalkyl of 3 to 10 carbon atoms, inclusive, aralkyl of 7 to 12 carbonatoms, inclusive, phenyl, phenyl substituted with one, two, or threechloro or alkyl of one to 3 carbon atoms, inclusive, or apharmacologically acceptable cation; and Wherein Z₈ is(1) --CH₂ --O--CH₂--(CH₂)_(g) --CH₂ --, (2) --(ch₂)₂ --o--(ch₂)_(g) --CH₂ --, or (3)--(CH₂)₃ --O--(CH₂)_(g) --,Wherein g is 1, 2, or
 3. 2. A compoundaccording to claim 1, wherein M₁ is ##STR6##
 3. A compound according toclaim 1, wherein M₁ is ##STR7##
 4. A compound according to claim 3,wherein Y is cis-CH═CH--.
 5. A compound according to claim 4, wherein mis
 3. 6. A compound according to claim 5, wherein g is
 3. 7.2a,2b-Dihomo-5-oxa-15-epi-cis-13-PGD₁, a compound according to claim 6.8. A compound according to claim 5, wherein g is
 1. 9.5-Oxa-15-epi-cis-13-PGD₁, a compound according to claim
 8. 10.3-Oxa-15-epi-cis-13-PGD₁, a compound according to claim
 8. 11. Acompound according to claim 3, wherein Y is trans-CH═CH--.
 12. Acompound according to claim 11, wherein m is
 3. 13. A compound accordingto claim 12, wherein Z₈ is

    --CH.sub.2 --O--CH.sub.2 --(CH.sub.2).sub.g --CH.sub.2 --.


14. a compound according to claim 13, wherein g is
 3. 15. A compoundaccording to claim 13, wherein g is
 1. 16. A compound according to claim15, wherein R₅ and R₆ are both hydrogen.
 17. A compound according toclaim 16, wherein R₃ and R₄ are both hydrogen.
 18. 5-Oxa-PGD₁, acompound according to claim
 17. 19. A compound according to claim 16,wherein R₃ and R₄ are both fluoro.
 20. 16,16-Difluoro-5-oxa-PGD₁, acompound according to claim
 19. 21. A compound according to claim 13,wherein Z₈ is

    --(CH.sub.2).sub.3 --O--(CH.sub.2).sub.g --.


22. A compound according to claim 21, wherein g is
 3. 23. A compoundaccording to claim 22, wherein R₅ and R₆ are both hydrogen.
 24. Acompound according to claim 23, wherein R₃ and R₄ are both hydrogen. 25.2a,2b-Dihomo-3-oxa-PGD₁, a compound according to claim
 24. 26. Acompound according to claim 23, wherein R₃ and R₄ are both fluoro. 27.2a,2b-Dihomo-16,16-difluoro-3-oxa-PGD₁, a compound according to claim24.
 28. A compound according to claim 21, wherein g is
 1. 29. A compoundaccording to claim 28, wherein R₅ and R₆ are both hydrogen.
 30. Acompound according to claim 29, wherein R₃ and R₄ are both hydrogen. 31.3-Oxa-PGD₁, a compound according to claim
 30. 32. A compound accordingto claim 29, wherein R₃ and R₄ are both fluoro. 33.16,16-Difluoro-3-oxa-PGD₁, a compound according to claim 32.